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Check availability on Winter Haven 5 Star Hotels

Our top choices for Winter Haven 5-star hotels

ette hotel

ette hotel
5.0 star property
Kissimmee
9.8 out of 10, Exceptional, (379)
"Great spa!"
United States
Claudette
The price is 11.344.396 ₫
12.875.890 ₫ total
includes taxes & fees
15 Jan - 16 Jan 2026
ette hotel

Encore Resort and Water Park at Reunion by Rentyl

Encore Resort and Water Park at Reunion by Rentyl
5.0 star property
Kissimmee
8.4 out of 10, Very good, (1001)
"Great staff! Very welcoming and accommodating."
Canada
Brian
The price is 6.554.676 ₫
18.793.230 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Encore Resort and Water Park at Reunion by Rentyl

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (1443)
"Wonderful staff"
United States
Joshua
Reunion Resort & Golf Club

The Bear's Den Resort Orlando

The Bear's Den Resort Orlando
5.0 star property
Reunion
8.0 out of 10, Very good, (22)
"Great place , I recommend it to everyone."
United States
Jacqueline
The Bear's Den Resort Orlando

Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Cozy 3Bd Close to Disney @ Enclaves at Festival 808
5.0 star property
Festival
6.8 out of 10, (3)
"Property was beautiful host was very attentive and answered all my questions and concerns area was safe and quiet the pool pass did not work was my only issue but everything else was top tier "
United States
Brittany
Cozy 3Bd Close to Disney @ Enclaves at Festival 808

Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

Family Friendly 2 Bd Close to Disney @ Champions Gate 8899
5.0 star property
Davenport
8.6 out of 10, Excellent, (8)
"They kept in contact the whole time we stayed with them. They responded to any questions promptly."
United States
Tiffany
Family Friendly 2 Bd Close to Disney @ Champions Gate 8899

7 Bedroom Villa, Private Pool, Resort Amenities

7 Bedroom Villa, Private Pool, Resort Amenities
5.0 star property
Kissimmee
8.6 out of 10, Excellent, (16)
"Beautiful and the family loved it 😍! Close to Disney, excellent for large families"
Canada
LLoyd
7 Bedroom Villa, Private Pool, Resort Amenities

WonderFull 4Bd with Pool at Champions Gate 1174

WonderFull 4Bd with Pool at Champions Gate 1174
5.0 star property
Davenport
9.0 out of 10, Wonderful, (4)
"This home was exactly as the pictures and more. It was beautiful and perfect size for my family. The pool was also perfect when we didn’t want to be in the crowds anymore at the resorts. Wonder vacation homes were amazing hosts and took great care of all of our questions "
United States
Anonymous traveller
WonderFull 4Bd with Pool at Champions Gate 1174

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Marvelous 3Bd w/ Pool Near Disney at Serenity 1536
5.0 star property
Clermont
8.8 out of 10, Excellent, (3)
"went with grandkids they enjoyed the dipping pool and area was nice and quiet. The place was very clean. "
United States
Esther
Marvelous 3Bd w/ Pool Near Disney at Serenity 1536

Gorgeous 5Bd Screened Pool at Champions Gate 1125

Gorgeous 5Bd Screened Pool at Champions Gate 1125
5.0 star property
Davenport
9.4 out of 10, Exceptional, (3)
"The house was exactly as the pictures posted. Very well maintained, cleaned, and well equipped with all essential equipment for cooking ext. My family and I loved it. It exceeded our expectations! We truly recommend this house, and will definitely rent this house again."
United States
Carmen
Gorgeous 5Bd Screened Pool at Champions Gate 1125

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

Stunning 5Bd w/ Pool @ Windsor Island Resort 3814
5.0 star property
Davenport
8.6 out of 10, Excellent, (8)
"Clean home. Pool and deck were great. Resort area was fun, clean and easy to use."
Canada
Suzanne
Stunning 5Bd w/ Pool @ Windsor Island Resort 3814

Gorgeous 4 Bedroom w/ Pool Close to Disney 920

Gorgeous 4 Bedroom w/ Pool Close to Disney 920
5.0 star property
Bellavida
8.0 out of 10, Very good, (2)
"The property is in need of repair and maintenance. I paid £240 for cleaning yet it didn’t look clean, for example, The carpets were sticky and there were hairs in the bathrooms. The location is good, but I wouldn’t call this a gorgeous property."
United Kingdom
selina
Gorgeous 4 Bedroom w/ Pool Close to Disney 920

Marvelous 7 Bd w/ Pool Close to Disney @ Solterra 6086

Marvelous 7 Bd w/ Pool Close to Disney @ Solterra 6086
5.0 star property
Solterra Resort
3.0 out of 10, (2)
"Horrible customer service. Pool was not heated also dirty once we arrived. Refrigerator was leaking. Bed felt like a sink hole. "
United States
Shanetha
Marvelous 7 Bd w/ Pool Close to Disney @ Solterra 6086

Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access
5.0 star property
Kissimmee
8.0 out of 10, Very good, (4)
"The house was huge we had enough room for everyone I loved the theme rooms and it was quiet "
United States
Tameko
Themed 7 Bedroom Villa, 12 Min to Disney, Resort Access

Amazing 4Bd Screened Pool Close to Disney 4572

Amazing 4Bd Screened Pool Close to Disney 4572
5.0 star property
Bellavida
8.0 out of 10, Very good, (5)
"The dryer didnt work and No Highchair , also never received my tickets to Water park with Lazy pool ticket. Other than that My Family enjoyed Everything. Pool is a Plus "
United States
Joseph
Amazing 4Bd Screened Pool Close to Disney 4572

Reunion Resort & Golf Club

Reunion Resort & Golf Club
5.0 star property
Reunion
8.8 out of 10, Excellent, (12)
"Enjoy the accommodations view was wonderful and close to everything"
United States
Anonymous traveller
Reunion Resort & Golf Club

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills
5.0 star property
Tuscan Hills
9.4 out of 10, Exceptional, (6)
"The unique rooms were a hit with our children."
United States
Joseph
Marvelous 4Bd Close to Disney w/ Pool at 313 Tuscan Hills

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158
5.0 star property
Davenport
9.8 out of 10, Exceptional, (6)
"Boyfriend and I chose here for our first vacation together and absolutely loved everything about the house we got! We sat by the private pool every day we were at the house and communication with the hosts was so easy and very reliable when needing a response We had a long drive and they accommodated us an early check-in no extra fee! Will 1000% stay here again when we return to Florida"
Canada
Emma
Stunning 4 Bd w/ Pool Close to Disney at Champions Gate 1158

Charming 3Bd Close to Disney @ Festival 1026

Charming 3Bd Close to Disney @ Festival 1026
5.0 star property
Festival
8.6 out of 10, Excellent, (4)
"Nice location "
United States
Jianzhuang
Charming 3Bd Close to Disney @ Festival 1026

Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub

Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub
5.0 star property
Davenport
Poolside At Calabay - Home for 11 With Game Room, Pool & Hot Tub
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Learn more about Winter Haven

Glide through LEGOLAND's colourful rides before cooling off at their water park on hot Florida afternoons. Chain of Lakes offers peaceful kayaking spots where you can paddle between waterways and spot wildlife at your own pace.

Winter Haven which includes rides

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Frequently asked questions

How much does it cost to stay in a 5-star hotel in Winter Haven?
There are a range of pricing options for 5-star hotels in Winter Haven on Expedia. How much you'll pay will depend on when you travel, length of your trip and other factors. Compare all of the available accommodation for your preferred dates and use our pricing and other filters to score the perfect high-end stay.

  • Search for the lowest price per night from 3.891.739 ₫

What makes a hotel 5 stars in Winter Haven?
From gourmet dining venues and all-day fitness centres to pools and the finest bedding, the 5-star experience in Winter Haven is all about indulgence and comfort. But it takes more than just top-notch conveniences to earn a 5-star rating. Stays must also offer outstanding guest-focused services like in-room massage treatments, laundry and dry cleaning and concierge services.
Are there any 5-star all-inclusive resorts in Winter Haven?
Our convenient filters are the quickest way to search for exactly what you're looking for. Check the "All inclusive" and "5-star" boxes to show the finest properties in Winter Haven where your meals, accommodation, entertainment and activities are included in the price. At these getaways, your trip is pure extravagance from the moment you enter the lobby.